Surrounded

Welcome to Surrounded, where one brave person faces twenty five. Every Sunday, dive into bold debates as a single guest takes on twenty five people with opposing views. No echo chambers, just raw, unfiltered conversations that challenge assumptions and spark connection.If you’re hungry for perspective, ready to wrestle with complexity, and believe in the power of debate, you’re in the right place. Subscribe now and join a community built on curiosity, empathy, and conversation that matters.

75 episodes

11d ago latest

weekly cadence

English language

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Episodes 76

1 Young Politician vs 20 Boomers (ft. Maxwell Frost) | Surrounded
7h ago · 1:54:01
Maxwell Frost takes center stage in Jubilee’s Surrounded, facing off against 20 Boomers to defend four hard-hitting claims: Gen Z is the most politically active generation in American history, they aren't too spoiled or lazy, all student debt should be canceled, and while Boomers lived the American Dream, Gen Z can only read about it. Can the youngest member of Congress hold his own against a room full of seasoned skeptics, or will the generational divide prove too wide to cross?
Tim Pool vs Progressives | Surrounded Follow-Up
11d ago · 56:28
Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 02:47 Clip 1 18:38 Clip 2 33:28 Clip 3 44:03 Clip 4
1 Moderate vs 20 Progressives (ft. Tim Pool)
14d ago · 1:40:32
Tim Pool steps into the ring with 20 progressives in this explosive episode of Jubilee’s Surrounded. Standing alone as the sole moderate voice, Pool defends four radical premises: the mainstream left commits more violence than the mainstream right, the Democratic Party has fully embraced authoritarianism, America is actively heading toward a civil war, and the U.S. Constitution effectively no longer exists. Will Tim withstand the crossfire, or will the consensus collapse his defense?
Is Trump Better for Black Americans Than Democrats? | Surrounded Follow-Up w/ Officer Tatum
21d ago · 1:02:20
On this week's episode, Officer Brandon Tatum joins host Parris Rose to recap Tatum's time in the Surrounded Circle. They discuss several clips with the guest debators, and break down some of the most heated moments of the discussion.
1 Black Conservative vs 20 Black Liberals (ft. Officer Tatum)
28d ago · 1:59:47
Officer Tatum steps into the center of Jubilee’s Surrounded to take on 20 Black Liberals in a high-stakes debate over race, politics, and responsibility. He stands alone to defend four explosive claims: Trump and the GOP are better for the Black community than Democrats, police do more good than harm, Black-on-Black crime is the most critical threat, and systemic racism is used as an excuse to avoid personal accountability. Will Tatum hold his ground under heavy fire, or will the panel dismantle his conservative playbook?
What Has The Manosphere Taught Us? | Surrounded Follow-Up
1mo ago · 50:23
Mark Manson steps outside the circle to unpack his debate with 20 manosphere creators. Is the manosphere helping men—or trapping them in an echo chamber of insecurity? What We Unpack in This Episode The Looksmaxxing Trap: Why hyper-focusing on superficial traits turns dating into a transaction—and leaves men feeling more isolated than ever. Echo Chambers vs. Reality: How the manosphere monetizes male insecurity and converts genuine loneliness into online hostility. The Middle School Mindset: Uncovering why so many digital "alphas" struggle to build lasting, adult relationships. Redefining Mode
1 Anti-Manosphere vs 20 Manosphere (ft. Mark Manson) | Surrounded
1mo ago · 1:24:29
Mark Manson steps into the circle against 20 manosphere creators in Jubilee’s Surrounded, defending four hard-hitting claims: the manosphere is a predatory business profiting off male anger, a woman's body count is irrelevant, porn has ruined men far more than feminism, and true attractiveness stems from respecting women. Will Manson dismantle the echo chamber with reason, or will the pack overrun him? They debate the 4 following claims that Mark Manson, has: 1. The manosphere is a business that profits off keeping men angry, 2. A woman's body count doesn't matter, 3. Porn has done more damage
How Can You Care But Not Vote? | Surrounded Follow-Up
1mo ago · 1:03:31
John Regalado sits down with non-voter Carlheb to unpack their recent Surrounded debate with Wes Moore. In this follow-up, they discuss the moral tension that comes with participating in an imperfect and often corrupt system, the legacy of slavery in the current political consciousness, the influence of black revolutionaries like Fred Hampton, and whether or not Wes Moore convince Carlheb to cast his vote in future elections.
Governor Wes Moore vs 20 Non-Voters | Surrounded
1mo ago · 1:21:47
Democratic leader Wes Moore faces 20 non-voters in a compelling episode of Surrounded, tackling political disillusionment head-on. He challenges the room with three urgent claims: 1) nothing shapes policy more effectively than your vote, 2) bad politics thrive when citizens don’t participate, and 3) abstaining from the ballot protects corruption rather than protesting it. Can Moore convince a skeptical crowd to reclaim their civic power, or will their disillusionment prove too deep to overcome?
Is Dean Alpha or Beta? | Surrounded Follow-Up
2mo ago · 1:04:33
John Regalado sits down with Lori and Julia Kate to unpack their viral Surrounded debate with Dean Withers. In this follow-up, they dive deeper into their personal backgrounds and values, their perspectives on Donald Trump, and discuss the discourse of modern political commentary.
Dean Withers vs 20 MAGA Women | Surrounded
2mo ago · 1:53:05
APPLY TO BE ON SURROUNDED: https://bit.ly/43MF3yZ Open General Casting Application: https://bit.ly/4xCliYn Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: / jubileemedia TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: / @lovecommanectar Instagram: / lovecommanectar Nectar app: https://lovecommanectar.co/m/download... ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com FEATURING Dean: / itsdeaann Tracey: / spartra Enya: / enyaschutsky Georgia: / georg
Is Dave Rubin Living in Reality? Surrounded Follow-Up
2mo ago · 42:13
Kyla Turner steps outside the circle to join John Regalado in this follow-up to the viral Dave Rubin Surrounded debate. In this discussion, Kyla shares her perspective on the debate – covering the perceived contradictions of Rubin's political alignment and identity, political extremism in American politics, economic metrics under the Trump administration and the necessity for political accountability and effective governance across the political spectrum.
Is Trump Losing Support For The War? | Surrounded Follow-Up
2mo ago · 41:13
Kikoff: Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!John Regalado sits down with Mat Nuclear to unpack his recent Surrounded debate with Glenn Greenwald. In this follow-up interview, John and Mat discuss the growing public sentiment against the United States' involvement in Iran, allegations of corruption within the Trump and Biden administrations, and who Mat sees as the potential political leaders for the 2028 election.
1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded
3mo ago · 1:40:14
Conservative commentator Dave Rubin enters the Surrounded circle to confront 20 far-left Democrats in an intense political showdown. In this episode, Rubin navigates a deeply hostile environment, defending four divisive claims: that "wokeism" has caused more damage to America than Donald Trump, that voting for Democrats in 2026 guarantees broken cities, schools, and borders, that progressives push moderate Americans to the right, and that the modern left prioritizes ideology over reality. Can Rubin’s blunt critiques challenge the room's core convictions?
1 Journalist vs 20 Trump Supporters (ft Glenn Greenwald) | Surrounded
3mo ago · 1:38:13
Independent journalist Glenn Greenwald steps into the circle to confront 20 MAGA supporters in a fiery political showdown. In this episode, Greenwald takes direct aim at the movement's core beliefs with four explosive claims: Trump’s legacy is defined by war rather than peace, his administration bows to the Israel lobby, his presidency was significantly more corrupt than Biden’s, and launching strikes on Iran would be a disaster for the American people. Will his relentless critiques force a reckoning, or can the room defend their champion?
Naima vs Charlie Kirk, 1 Year Later | Surrounded Follow-Up
3mo ago · 1:17:53
John Regalado sits down with recurring Surrounded guest, Naima, to look back at some of her most memorable moments from the Surrounded circle. In this special episode, Naima and John discuss whether Charlie Kirk's assassination changed how she views debate, what it was like to become a political persona overnight, and if she stand by her debate tactics with Charlie Kirk and Ben Shapiro.
1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded
3mo ago · 1:31:20
Kikoff: Build credit fast and get your first month for just a dollar at getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Psychiatrist Dr. K sits down with 20 individuals battling depression in a raw and deeply personal conversation about the realities of mental health. In this episode of Surrounded, Dr. K navigates profound emotional divides, defending four core claims: you are overwhelmed rather than broken, hopelessness is a symptom not a final conclusion, deep depression can coexist with productivity and success, and past therapy failures don’t mean you are beyond help.
Israeli vs Palestinian: Can They Agree? | Surrounded Follow-up (ft. Rudy Rochman and Dr. Ahmed Soboh)
3mo ago · 1:01:08
John Regalado is joined by Rudy Rochman and Dr. Ahmed Soboh to revisit their recent Surrounded debate about the Israeli-Palestinian conflict. In this follow-up, they discuss religious extremism on both sides of the conflict, what major compromises both Rudy and Ahmed would consider acceptable in order to achieve peace, and if a one state solution for all could actually be achievable.
1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded
4mo ago · 1:48:35
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us! Jewish and Israel rights activist Rudy Rochman rights activist Rudy Rochman faces 20 pro-Palestinian advocates in a deeply emotional and urgent debate over the Israeli-Palestinian conflict. In this episode of Surrounded, Rochman defends four core claims: that Israel is not committing genocide or apartheid, that anti-Zionism equates to anti-Semitism, that Jews are indigenous to Israel, and that Zionism is a movement of decolonization. As historical trauma m
Why a Conservative and Liberal Agree on the Epstein Files | Surrounded Follow-Up
4mo ago · 1:00:36
John Regalado sits down with Andrew (Liberal) and Marien (Conservative) from Ro Khanna’s Epstein Files Surrounded debate to unpack the fallout. They revisit why the Epstein Transparency Act fell short, whether holding the “Epstein class” accountable has become empty political rhetoric, and if Marien’s loyalty to Trump has shifted at all.
1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded
4mo ago · 1:22:15
Representative Ro Khanna enters the circle to face 20 Americans in a high-stakes debate about power, privilege, and the Epstein files. In this episode of Surrounded, Khanna navigates a deeply polarizing political landscape, defending four uncompromising claims: that America's justice system is two-tiered, the DOJ is illegally withholding crucial files, Commerce Secretary Howard Lutnick must resign, and the U.S. must finally hold its powerful elites accountable. In a space where demands for political transparency clash with fractured public trust, can Khanna find common ground with his critics?
Why Are Vegans So Annoying? | Jack Symes Surrounded Follow-up
4mo ago · 1:04:36
Philosopher and author Dr. Jack Symes and John Regalado meet again to dissect Jack's Surrounded debate with 20 meat eaters. In this follow-up, they examine the moral weight of animal suffering, the scientific data behind plant-based longevity, and the controversial argument that modern food systems constitute a global moral crisis.
1 Vegan vs 20 Meat Eaters (ft. Jack Symes)
4mo ago · 1:38:20
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Vegan advocate Jack Symes enters the circle to face 20 meat-eaters in an intense debate about the ethics of our diets. In this episode of Surrounded, Symes navigates a deeply polarizing landscape, defending four uncompromising claims: that extreme suffering for trivial pleasure is morally indefensible, that everyone should aim to be vegan, that factory farming ranks among the worst atrocities in history, and that veganism is fundamentally good for the world
Top 5 Most Heated Debates | Surrounded
5mo ago · 29:02
In this compilation episode of Surrounded, we revisit the most explosive and polarizing debates of the past year. One by one, these guests stepped into the circle to face 20 opposing voices in high-stakes clashes. Watch as Sam Seder takes on conservatives over DEI, Candace Owens defends traditional motherhood against feminists, Jordan Peterson clashes with atheists over morality and purpose, and more.
Is Body Positivity Disempowering? Follow-up (ft. Jillian Michaels) | Surrounded
5mo ago · 54:28
Fitness icon Jillian Michaels sits down with John Regalado and body positivity advocate Marcy Guevara to unpack the emotional fallout from her Surrounded debate. In this follow-up, they dive into the "primary wound" of childhood trauma, the conflict between movement loyalty and personal health, and why Jillian believes identifying as "fat" can become a psychological prison that hinders true liberation.